Methylhydrazine → HCID 67120036, compound

HRID 1410162Notes

Reaction equation

HRID 1410162 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=O)=[CH:5][CH:4]=1.[CH2:12]([OH:16])[CH2:13][C:14]#[CH:15].C(N(CC)CC)C.[CH3:24][NH:25][NH2:26]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(O)(=O)C.CO.C1COCC1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[CH:15]=[C:14]([CH2:13][CH2:12][OH:16])[N:25]([CH3:24])[N:26]=2)=[CH:5][CH:4]=1

Participants

10

Reactant 4

HCID 6061MethylhydrazineHCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 135663-Butyn-1-OL

Product 1

HCID 67120036HCID 67120036, compoundYield 74%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

PdCl2(PPh3)2 (14.0 mg, 0.02 mmol) and CuI (7.6 mg, 0.04 mmol) was added to dry THF (2 mL) and degassed. 4-Methoxybenzoic chloride (171 mg, 1.0 mmol), but-3-yn-1-ol (77.1 mg, 1.1 mmol) and triethylamine (292 μL, 1.1 mmol) were added to the mixture and stirred at room temperature for 1 h. Methylhydrazine (50.7 mg, 1.1 mmol) was added to the reaction mixture together with MeOH (0.5 mL) and acetic acid (0.5 mL) and the mixture was irradiated in the microwave at 150° C. for 10 min. The solution was concentrated and purified on silica gel to give 2-(3-(4-methoxyphenyl)-1-methyl-1H-pyrazol-5-yl)ethanol (173 mg, 0.74 mmol, 74%).

Workup

  1. customdegassed
  2. customthe mixture was irradiated in the microwave at 150° C. for 10 min
  3. concentrationThe solution was concentrated
  4. custompurified on silica gel

Sources & evidence

ORD record
ord-f26ecc0c195247c08e882a4b72ca97aa
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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